Reactions of (per)fluorinated peroxides, in particular of (per)fluoroalkanoylperoxides, with organic compounds are well known in the art. Thus, (per)fluorinated peroxides like (per)fluoroalkanoylperoxides have been found to represent suitable tools for the introduction of fluoroalkyl groups into various organic molecules, generally with formation of a carbon-carbon bond.
Direct (per)fluoroalkylation of aromatic substrates, which is generally not achievable via standard methodologies (i.e. Friedel-Craft), can thus be obtained with success through a radical reaction pathway by means of suitable perfluoroalkyl radicals. These synthetic pathways have been recognized to provide with substitution reaction at the aromatic moiety.
It is also known that polyfluorinated aromatic compounds generally undergo addition reactions when reacted with (fluoro)organic radicals. Thus, KOBRINA, L. S. Some perculiarities of radical reactions of polyfluoroaromatic compounds. J. Fluor. Chem. 1989, vol. 42, p. 301-344. discloses reaction mechanism and adducts obtained from reactions of free radicals (including fluorinated radicals) onto perfluorobenzene, perfluorotoluene, perfluoronaphtalene.
Similarly, BROOKE, Gerald M. The preparation and properties of polyfluoro aromatic and heteroaromatic compounds. J. Fluor. Chem. 1997, vol. 86, p. 1-76. teaches addition reactions of certain organic radicals onto fluoroaromatic compounds.
Nevertheless, these investigations were limited to certain (per)fluoroalkyl or (per)fluoroalkanoylperoxides, and addition compounds thereof onto fluoroaromatic nuclei were merely investigated for mechanistic purposes.
It has now been surprisingly found that the reaction between certain fluorinated peroxides with organic compounds comprising per(halo)fluorinated aromatic moieties yields addition products comprising at least two fluorinated residues which have been notably found useful as additives for (per)fluorinated fluids and lubricants or as base materials for the manufacture of gum and/or graft polymer compositions.